(S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate

Base Information

• Chemical Name: (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate
• CAS No.: 1581755-92-1
• Molecular Formula: C₂₅H₂₄N₂O₅S
• Molecular Weight: 464.542

Synonyms:(S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate

Chemical Property of (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate

Chemical Property:

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Technology Process of (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate

There total 4 articles about (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(S)-6-(hydroxymethyl)-4-(4-methoxyphenylethynyl)-N-(1-phenylethyl)-picolinamide (1581755-88-5) + methanesulfonyl chloride (124-63-0) → (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate (1581755-92-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 5 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c3dt53000k

Reference yield:

methyl 6-(hydroxymethyl)-4-iodopicolinate (1247012-08-3) → (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate (1581755-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / water; ethanol / 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; dichloromethane / 22 h / 20 °C / Inert atmosphere

3: triethylamine; copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / 65 °C / Inert atmosphere

4: triethylamine / tetrahydrofuran / 0.5 h / 5 - 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;

DOI:10.1039/c3dt53000k

Reference yield:

6-(hydroxymethyl)-4-iodopicolinic acid (1581755-84-1) → (S)-(4-(4-methoxyphenylethynyl)-6-(1-phenylethylcarbamoyl)pyridine-2-yl)methyl methanesulfonate (1581755-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; dichloromethane / 22 h / 20 °C / Inert atmosphere

2: triethylamine; copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / 65 °C / Inert atmosphere

3: triethylamine / tetrahydrofuran / 0.5 h / 5 - 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1039/c3dt53000k

upstream raw materials:

(S)-6-(hydroxymethyl)-4-(4-methoxyphenylethynyl)-N-(1-phenylethyl)-picolinamide

methanesulfonyl chloride

methyl 6-(hydroxymethyl)-4-iodopicolinate

6-(hydroxymethyl)-4-iodopicolinic acid

Downstream raw materials:

6,6',6''-((1,4,7-triazacyclononane-1,4,7-triyl)tris(methylene))tris(4-((4-methoxyphenyl)ethynyl)-N-((S)-1-phenylethyl)-picolinamide)

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